From the Coach's Chair: 37 Lessons, 37 Dreams
Here’s What Brought Me to the Chair Today
In just two days, I’ll be turning 37. And instead of spiraling into a crisis about being officially “late 30s,” I decided to sit down and reflect—on what’s shaped me, stretched me, and made life really worth living so far.
Some moments are huge and unforgettable. Others are quiet but powerful. All of them are part of my story. And because I’m always dreaming bigger, I’m also sharing 37 things I still want to do—goals, adventures, and maybe a little chaos for good measure.
So, here we go: 37 moments I’ve lived, 37 dreams I’m chasing.
37 of My Greatest Moments
1) Getting our first family dog, Bridget, when I was four—while trying to keep up with her on a broken leg from a horrific curly slide incident.
2) My 8th birthday—the only birthday where I had a party with school friends. My “boyfriend” got me the Goosebumps board game.
3) In fifth grade, my friends and I started a witches’ coven called Forces of Nature. We did rain dances on the kickball field during recess… and it usually worked.
4) Also in fifth grade, my “boyfriend” got me a cassette tape organizer for Christmas because I didn’t have a CD player yet.
5) Sixth grade was rough—my elementary friends pushed me aside, but middle school brought new friendships. Steff and I have been BFFs ever since.
6) Had my first kiss at a school dance in eighth grade (I think?). Then spent the weekend at Steff’s mom’s house—always a blast.
7) Had a major glow-up between seventh and eighth grade—braces off, clearer skin, and feeling more confident. Even my middle school bully stopped being mean to me!
8) Briefly dated the senior next door in ninth grade. It was weird. That ended quickly, thank goodness.
9) Spent weekends with Steff, and on New Year’s Eve freshman year, I may have made out with her cousin in the closet. (She knows, no secrets here!)
10) Good Charlotte played in our high school gym after we won KDWB’s Pennies for Heaven contest. It was epic!
11) Met my high school boyfriend over Memorial Day weekend at my cabin while cruising around on golf carts.
12) Made some amazing new friends in sophomore year—one of whom was my best friend through the rest of high school.
13) Took a trip to Maryland with my aunt, built a relationship with my cousins, and had a blast.
14) Junior year study hall squad—we got permission to watch movies in our teacher’s classroom on the projector.
15) Was named World Language Student of the Month (thanks, Madame Dahlberg!).
16) Discovered a love for creative writing—I’m sure my teacher worried about some of my darker stories, but it was an outlet I needed.
17) Read Stephen King’s IT for my high school Mystery & Horror class. That book was thick, but I was hooked!
18) Got my first job as a server at IHOP, then switched to Circuit City for better pay.
19) Lettered in academics all four years of high school.
20) Started college at Century Community College for Business Management.
21) Got engaged to my high school boyfriend, complete with matching ring tattoos. (Let’s just say… lesson learned.)
22) Finally ended that relationship during my second year of college—definitely a pivotal moment.
23) Graduated college with an Associate’s Degree in Business Management.
24) Got a job at Apple—which introduced me to some truly amazing people and became one of the biggest pivots in my life.
25) Moved into my first apartment with a roommate. Let’s just say… interesting experience.
26) Discovered I had fibromyalgia, lost my job with Target (thank goodness), and had to adjust to my new reality.
27) Met Dan—and knew immediately that I was going to marry him someday.
28) Lost my job due to my health and had to move back home—one of the lowest but also most transformative times in my life.
29) Dan and I moved in together again, marking a new chapter.
30) Took our first cruise together and fell in love with traveling this way!
31) Got a job in childcare, which completely changed my career path.
32) Welcomed our son, Garon, into the world.
33) Bought our forever home after the craziness of 2020 and COVID.
34) Finally got engaged after nine years together.
35) Welcomed our daughter, Jorie, into the world.
35) Welcomed our daughter, Jorie, into the world.
36) Got married and said I do to forever.
37) Discovered my love for health and wellness, leading me to my next adventure—becoming a Health & Wellness Coach.
37 Things I Will Achieve in the Next 37 Years
Become a certified Health & Wellness Coach
Travel to Europe
Travel to Australia
Visit all 50 states
Solo travel more
Take the kids to Israel
Convert to Judaism
Learn Hebrew (not just reading, but speaking!)
Travel more with the kids
See the National Parks
Get a cabin
Own a house somewhere warm for the winters
Buy a home in Bonaire to retire to
Finish our basement for the ultimate women’s cave
Be a surrogate
Do foster care
Read 2,000 books
Start a podcast
Write and publish a book
Coach 1,000 people
Volunteer in my community
Go on a retreat
Host my first retreat
Build and run a retreat space
Renew our wedding vows on a cruise
Watch Garon’s bar mitzvah
Watch Jorie’s bat mitzvah
Go on an Alaskan cruise
Go on a Transatlantic cruise
Learn to drive a manual car (for when I’m on The Amazing Race—if that show still exists!)
Keep fostering relationships with those closest to me
Go to Vegas
Experience Mardi Gras
Go to Burning Man (but only if it’s the original version, not the commercialized one)
Become a grandmother and be active in my grandkids’ lives
Start support groups for moms and teen daughters
Own a VW Buzz minivan (because why not?)
Your Turn: Reflect, Remember, Dream
Some of these moments might seem small, but they were pivotal in shaping who I am. And looking ahead, I can’t wait to keep growing, learning, and checking off these bucket list items.
What are some of your greatest memories? And what’s on your bucket list for the next stage of your life? Drop them in the comments!
XOXO,
Jessica